Synthesis and electronic absorption spectra of substituted tetrabenzoporphins

Zinc complexes of tetrabenzoporphins with substituents in the benzene fragments of the molecule were synthesized by the template tetramerization of substituted 3-carboxymethylphthalimidines or phthalimides with malonic or phenylacetic acid in the presence of zinc acetate, as well as by substitution reactions in the tetrabenzoporphin molecule. The metal-free compounds were obtained from the corresponding zinc complexes by the action of a stream of hydrogen chloride in chloroform. The electronic absorption spectra of the synthesized compounds were investigated.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 773–779, June, 1988.     

Synthesis of meso-tetraalkyltetrabenzoporphines

Stable complexes of zinc meso-tetralkyltetrabenzoporphines with tribenzylamine have been obtained by the template tetramerization of 3-R-methylenephthalimidines with zinc acetate in the presence of tribenzylamine or by the reaction of potassium phthalimide with the corresponding alkylmalonic acids. The structures of the compounds synthesized have been confirmed by their electronic absorption spectra, and in some cases also by their mass spectra.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 61–64, January, 1984.     

Triplet-triplet absorption spectra of meso-tetraphenyl-2,3-tetranaphtho-2,3-tetraphenanthroporphins

Flash photolysis has been used to measure triplet-triplet (T-T) absorption spectra of meso-tetrapheny1-2,3-tetranaphthorphin and its zinc complex, and also zinc complexes of two isomers of meso-tetrapheny1-2,3-tetraphenanthrenopurphin. An analysis has been made of the inf Iuence of structural changes on the T-T absorption spectra.Institute of Physics, Academy of Sciences of the Belorussian SSR, Minsk. Scientific-Research Institute of Organic Intermediates and Dyestuffs, Moscow. Translated from Teoreticheskaya i Éksperimental'naya Khimiya, No. 1, pp. 105–108, January–February, 1991. Original article submitted February 24, 1989.     

Unsaturated chloro-substituted dinitriles in the synthesis of porphyrazines

Chloro- and alkoxy-substituted porphyrazines were obtained in the reaction of mono- and dichloromaleo (fumaro)nitriles with metal chlorides or alkoxides. The structures of the synthesized compounds were confirmed by their electronic absorption spectra.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1645–1646, December, 1982.     

Unsymmetrical tetraarenoporphines

Zinc complexes of unsymmetrical tetraarenoporphines and their oxidized forms were synthesized by condensation of mixtures of phthalic and naphthalene-2,3-dicarboxylic acid imides with sodium acetate or malonic acid in the presence of zinc acetate. Metal-free compounds were obtained by treatment of benzene solutions of the zinc complexes with gaseous hydrogen chloride. The electronic, PMR, x-ray electron, IR, and mass spectra of the synthesized compounds are discussed.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1351–1357, October, 1988.     

Synthesis of mono- and disubstituted tetra(tert-butyl)porphyrazines

Bromination of tetra(tert-butyl)porphyrazine by N-bromosuccinimide in chloroform results in the formation of mono- and dibromides, substitution for the bromine atoms of which produced the corresponding cyano, phenoxy, phenylthio, styryl, phenylethynyl and piperidino derivatives. From the monobromide and 2,2-bis(p-hydroxyphenyl)propane, the dimeric porphyrazine 2,2-bis[p-tetra(tert-butyl)porphyrazyloxyphenyl]propane was similarly obtained.Scientific Research Institute of Organic Intermediate Products and Dyes, Moscow 103787. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1206–1212, September, 1994. Original article submitted September 6, 1994.     

New isoindologens in the synthesis of tetrabenzoporphins

Isoindoline hydrochloride reacts with paraformaldehyde, mesoxalic acid hydrate, N-methylformanilide, diphenylformamide, and methylene iodide in the presence of zinc acetate to give zinc tetrabenzoporphin and with sodium phenylacetate or tribenzylamine to give zinc meso-tetraphenyltetrabenzoporphin. These products are formed, respectively, from o-formylbenzoic acid and ammonium salts of malonic and phenylacetic acids. 1-Imino derivatives of isoindoline react with malonic acid to give mixtures that contain the corresponding tetrabenzoporphins, their mono- and triaza derivatives, and phthalocyanines.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1372–1377, October, 1985.